US9213248B2 - Latex comprising colorant and methods of making the same - Google Patents
Latex comprising colorant and methods of making the same Download PDFInfo
- Publication number
- US9213248B2 US9213248B2 US13/949,195 US201313949195A US9213248B2 US 9213248 B2 US9213248 B2 US 9213248B2 US 201313949195 A US201313949195 A US 201313949195A US 9213248 B2 US9213248 B2 US 9213248B2
- Authority
- US
- United States
- Prior art keywords
- latex
- colorant
- styrene
- monomer
- acrylate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000003086 colorant Substances 0.000 title claims abstract description 101
- 239000004816 latex Substances 0.000 title claims abstract description 85
- 229920000126 latex Polymers 0.000 title claims abstract description 85
- 238000000034 method Methods 0.000 title claims abstract description 40
- 239000000178 monomer Substances 0.000 claims abstract description 43
- 229920000642 polymer Polymers 0.000 claims abstract description 32
- 230000008569 process Effects 0.000 claims abstract description 29
- 239000002105 nanoparticle Substances 0.000 claims abstract description 18
- 125000000524 functional group Chemical group 0.000 claims abstract description 13
- 125000000129 anionic group Chemical group 0.000 claims abstract description 11
- 230000000379 polymerizing effect Effects 0.000 claims abstract description 4
- 239000002245 particle Substances 0.000 claims description 84
- 239000000049 pigment Substances 0.000 claims description 43
- 235000000177 Indigofera tinctoria Nutrition 0.000 claims description 25
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 claims description 25
- 229940097275 indigo Drugs 0.000 claims description 24
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 20
- 239000003795 chemical substances by application Substances 0.000 claims description 18
- 239000004094 surface-active agent Substances 0.000 claims description 17
- 239000000654 additive Substances 0.000 claims description 14
- 150000002500 ions Chemical class 0.000 claims description 14
- 229920001577 copolymer Polymers 0.000 claims description 11
- 238000006116 polymerization reaction Methods 0.000 claims description 11
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 10
- 230000004931 aggregating effect Effects 0.000 claims description 10
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 9
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 7
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 4
- 230000000996 additive effect Effects 0.000 claims description 4
- 239000012986 chain transfer agent Substances 0.000 claims description 4
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 239000004971 Cross linker Substances 0.000 claims description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 3
- 229910019142 PO4 Inorganic materials 0.000 claims description 3
- 150000007942 carboxylates Chemical class 0.000 claims description 3
- 238000011068 loading method Methods 0.000 claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 239000000839 emulsion Substances 0.000 abstract description 29
- -1 alkyl quaternary ammonium salt Chemical class 0.000 description 109
- 239000001993 wax Substances 0.000 description 33
- 239000000203 mixture Substances 0.000 description 32
- 241001062009 Indigofera Species 0.000 description 24
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 20
- 125000000217 alkyl group Chemical group 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 239000006185 dispersion Substances 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 13
- 238000007720 emulsion polymerization reaction Methods 0.000 description 13
- 230000002776 aggregation Effects 0.000 description 12
- 239000000975 dye Substances 0.000 description 12
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 238000004220 aggregation Methods 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 239000003999 initiator Substances 0.000 description 10
- 229910001868 water Inorganic materials 0.000 description 10
- CRDNMYFJWFXOCH-YPKPFQOOSA-N (3z)-3-(3-oxo-1h-indol-2-ylidene)-1h-indol-2-one Chemical compound N/1C2=CC=CC=C2C(=O)C\1=C1/C2=CC=CC=C2NC1=O CRDNMYFJWFXOCH-YPKPFQOOSA-N 0.000 description 9
- 239000000701 coagulant Substances 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- JOUDBUYBGJYFFP-NXVVXOECSA-N (2z)-2-(3-oxo-1-benzothiophen-2-ylidene)-1-benzothiophen-3-one Chemical compound S/1C2=CC=CC=C2C(=O)C\1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-NXVVXOECSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 8
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 239000008367 deionised water Substances 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- 235000019270 ammonium chloride Nutrition 0.000 description 6
- 239000003093 cationic surfactant Substances 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000011159 matrix material Substances 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- ZWQBZEFLFSFEOS-UHFFFAOYSA-N 3,5-ditert-butyl-2-hydroxybenzoic acid Chemical compound CC(C)(C)C1=CC(C(O)=O)=C(O)C(C(C)(C)C)=C1 ZWQBZEFLFSFEOS-UHFFFAOYSA-N 0.000 description 5
- CRDNMYFJWFXOCH-BUHFOSPRSA-N Couroupitine B Natural products N\1C2=CC=CC=C2C(=O)C/1=C1/C2=CC=CC=C2NC1=O CRDNMYFJWFXOCH-BUHFOSPRSA-N 0.000 description 5
- 239000004743 Polypropylene Substances 0.000 description 5
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 5
- 229940027983 antiseptic and disinfectant quaternary ammonium compound Drugs 0.000 description 5
- 238000004581 coalescence Methods 0.000 description 5
- 229910021641 deionized water Inorganic materials 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 238000009826 distribution Methods 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- 230000004048 modification Effects 0.000 description 5
- 238000012986 modification Methods 0.000 description 5
- 239000002736 nonionic surfactant Substances 0.000 description 5
- 229920001155 polypropylene Polymers 0.000 description 5
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 5
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 5
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 5
- 229910052725 zinc Inorganic materials 0.000 description 5
- 239000011701 zinc Substances 0.000 description 5
- NDDLLTAIKYHPOD-ISLYRVAYSA-N (2e)-6-chloro-2-(6-chloro-4-methyl-3-oxo-1-benzothiophen-2-ylidene)-4-methyl-1-benzothiophen-3-one Chemical compound S/1C2=CC(Cl)=CC(C)=C2C(=O)C\1=C1/SC(C=C(Cl)C=C2C)=C2C1=O NDDLLTAIKYHPOD-ISLYRVAYSA-N 0.000 description 4
- MLCPSWPIYHDOKG-BUHFOSPRSA-N (3e)-3-(2-oxo-1h-indol-3-ylidene)-1h-indol-2-one Chemical compound O=C\1NC2=CC=CC=C2C/1=C1/C2=CC=CC=C2NC1=O MLCPSWPIYHDOKG-BUHFOSPRSA-N 0.000 description 4
- 0 CC.CC.[1*]N([2*])C.[1*]N([2*])[3*] Chemical compound CC.CC.[1*]N([2*])C.[1*]N([2*])[3*] 0.000 description 4
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- WIZRPQYWANTMOT-BUHFOSPRSA-N Diosindigo Chemical compound C/1=C(OC)C2=CC(C)=CC(O)=C2C(=O)C\1=C1/C=C(OC)C2=CC(C)=CC(O)=C2C1=O WIZRPQYWANTMOT-BUHFOSPRSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 239000004698 Polyethylene Substances 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 229910052804 chromium Inorganic materials 0.000 description 4
- 239000011651 chromium Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- QNLOWBMKUIXCOW-UHFFFAOYSA-N indol-2-one Chemical compound C1=CC=CC2=NC(=O)C=C21 QNLOWBMKUIXCOW-UHFFFAOYSA-N 0.000 description 4
- FGFUBBNNYLNVLJ-UHFFFAOYSA-N indol-3-one Chemical compound C1=CC=C2C(=O)C=NC2=C1 FGFUBBNNYLNVLJ-UHFFFAOYSA-N 0.000 description 4
- 238000005342 ion exchange Methods 0.000 description 4
- 229910052742 iron Inorganic materials 0.000 description 4
- CRDNMYFJWFXOCH-UHFFFAOYSA-N isoindigotin Natural products N1C2=CC=CC=C2C(=O)C1=C1C2=CC=CC=C2NC1=O CRDNMYFJWFXOCH-UHFFFAOYSA-N 0.000 description 4
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
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- 239000001294 propane Substances 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- UOZOCOQLYQNHII-UHFFFAOYSA-N 6-bromo-2-(6-bromo-3-hydroxy-1H-indol-2-yl)indol-3-one Chemical compound [O-]c1c([nH]c2cc(Br)ccc12)C1=[NH+]c2cc(Br)ccc2C1=O UOZOCOQLYQNHII-UHFFFAOYSA-N 0.000 description 3
- 239000002028 Biomass Substances 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 3
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
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- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 3
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- 125000003545 alkoxy group Chemical group 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 239000003945 anionic surfactant Substances 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 3
- 229910052793 cadmium Inorganic materials 0.000 description 3
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
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- 239000006229 carbon black Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- UCYFZDNMZYZSPN-UHFFFAOYSA-N docosyl(trimethyl)azanium Chemical compound CCCCCCCCCCCCCCCCCCCCCC[N+](C)(C)C UCYFZDNMZYZSPN-UHFFFAOYSA-N 0.000 description 3
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- VKWNTWQXVLKCSG-UHFFFAOYSA-N n-ethyl-1-[(4-phenyldiazenylphenyl)diazenyl]naphthalen-2-amine Chemical compound CCNC1=CC=C2C=CC=CC2=C1N=NC(C=C1)=CC=C1N=NC1=CC=CC=C1 VKWNTWQXVLKCSG-UHFFFAOYSA-N 0.000 description 3
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- 229910052707 ruthenium Inorganic materials 0.000 description 3
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- 150000003871 sulfonates Chemical class 0.000 description 3
- 229910052715 tantalum Inorganic materials 0.000 description 3
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 3
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- ADHAJDDBRUOZHJ-UHFFFAOYSA-N 1-benzothiophen-3-one Chemical compound C1=CC=C2C(=O)CSC2=C1 ADHAJDDBRUOZHJ-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- ARTAFUJPRUWRJK-UHFFFAOYSA-N 3h-1-benzothiophen-2-one Chemical compound C1=CC=C2SC(=O)CC2=C1 ARTAFUJPRUWRJK-UHFFFAOYSA-N 0.000 description 2
- LRBZENFZSJNJCR-UHFFFAOYSA-N 5-bromo-2-(5-bromo-3-hydroxy-1H-indol-2-yl)indol-3-one Chemical compound [O-]c1c([nH]c2ccc(Br)cc12)C1=[NH+]c2ccc(Br)cc2C1=O LRBZENFZSJNJCR-UHFFFAOYSA-N 0.000 description 2
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- FMQQGWMGTKBWHR-UHFFFAOYSA-N 8-hydroxy-2-(8-hydroxy-6-methyl-1,4-dioxonaphthalen-2-yl)-6-methylnaphthalene-1,4-dione Chemical compound CC1=CC(O)=C2C(=O)C(C=3C(=O)C4=C(O)C=C(C=C4C(=O)C=3)C)=CC(=O)C2=C1 FMQQGWMGTKBWHR-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/087—Binders for toner particles
- G03G9/08702—Binders for toner particles comprising macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- G03G9/08737—Polymers derived from conjugated dienes
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/09—Colouring agents for toner particles
- G03G9/0906—Organic dyes
- G03G9/0912—Indigoid; Diaryl and Triaryl methane; Oxyketone dyes
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/093—Encapsulated toner particles
- G03G9/09307—Encapsulated toner particles specified by the shell material
- G03G9/09314—Macromolecular compounds
- G03G9/09321—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/093—Encapsulated toner particles
- G03G9/0935—Encapsulated toner particles specified by the core material
- G03G9/09357—Macromolecular compounds
- G03G9/09364—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/093—Encapsulated toner particles
- G03G9/0935—Encapsulated toner particles specified by the core material
- G03G9/09378—Non-macromolecular organic compounds
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/093—Encapsulated toner particles
- G03G9/09392—Preparation thereof
Definitions
- Embodiments disclosed herein relate to latexes used in the manufacture of toner particles. More particularly, embodiments disclosed herein relate to processes and compositions used for integrating optionally modified colorants into the matrix of polymer particles in a latex.
- Colorants such as dyes and pigments, employed in toner particle synthesis are typically added during the aggregation and coalescence (EA/coalescence) of a latex comprising toner particles.
- Natural pigments such as indigo, are potentially useful colorants but are often difficult to disperse due to their large particle size and lack of functionality. These characteristics may also make dispersant attachment to the pigment particle challenging.
- esterquats include, but are not limited to, esterquats such as those available from Kao Chemicals Inc., quaternary ammonium salts of: reacted fatty acids, C10-C20 and unsaturated C16-C18, with triethanolamine (CAS No. 91995-81-2), reacted tallow fatty acids with triethanolamine (CAS No. 93334-15-7), reacted fatty acids, C12-C20 with triethanolamine (CAS No. 91032-11-0), reacted 9-octadecenoic acid (Z) with triethanolamine (CAS No. 94095-35-9), reacted octadecenoic acid with triethanolamine (CAS No. 85408-12-4).
- esterquats such as those available from Kao Chemicals Inc., quaternary ammonium salts of: reacted fatty acids, C10-C20 and unsaturated C16-C18, with triethanolamine (CAS No. 91995-81-2), reacted tallow
- azoamidine compounds for example 2,2′-azobis(2-methyl-N-phenylpropionamidine)dihydrochloride, 2,2′-azobis[N-(4-chlorophenyl)-2-methylpropionamidine]di-hydrochloride, 2,2′-azobis[N-(4-hydroxyphenyl)-2-methyl-propionamidine]dihydrochloride, 2,2′-azobis[N-(4-amino-phenyl)-2-methylpropionamidine]tetrahydrochloride, 2,2′-azobis[2-methyl-N(phenylmethyl)propionamidine]dihydrochloride, 2,2′-azobis[2-methyl-N-2-propenylpropionamidine]dihydrochloride, 2,2′-azobis[N-(2-hydroxy-ethyl)-2-methylpropionamidine]dihydrochloride, 2,2′-azobis[2(5-methyl-2-azobis(2-methyl-phenylpropion
Abstract
Description
TABLE 1 | |
Indigo |
|
Isoindigo |
|
Indirubine |
|
Isoindirubine |
|
4,4′-dibromo indigo |
|
6,6′-dibromo indigo |
|
5,5′-dibromo indigo |
|
cis-6,6′-dibromo indirubin |
|
5,5′,7,7′- tétrabromo indigo |
|
4,4′,7,7′- tétrachloroindigo |
|
3H-Indol-3-one, 1,2-dihydro-2-(3-oxobenzo[b]thien-2(3H)- ylidene) |
|
Thioindigo (also called: C.I. 73300 C.I. Disperse Red 364 C.I. Solvent Red 242 C.I. Vat Red 41 Ciba Pink B Disperse Red 364) |
|
Vat Red 1 (Oralith) |
|
Cis-Thioindigo (Benzo[b]thiophen-3(2H)-one, 2-(3-oxobenzo[b]thien-2(3H)-ylidene)-,(2Z)) |
|
6,6′-dichloro- 4,4′-diméthylindigo |
|
5,5′-dichloro- 7,7′-diméthylindigo |
|
4,4′,7,7′- tétraméthylindigo |
|
Thioindigo Scarlet R (also known as: 2H-Indol-2-one, 1,3-dihydro-3-(3-oxobenzo[b]thien-2(3H)- ylidene; C.I. 73635) |
|
2H-lndol-2-one, 1,3-dihydro-3-(3-oxobenzo[b]thien-2(3H)- ylidène)-, (3E)- |
|
Thioindirubine (Benzo[b]thiophen-3(2H)-one, 2-(2-oxobenzo[b]thiophen-3(2H)-ylidene)) |
|
2H-Indol-2-one, 1,3-dihydro-3-(2-oxobenzo[b]thiophen-3(2H)- ylidene)- |
|
Benzo[b]thiophen-2(3H)-one, 3-(2-oxobenzo[b]thiophen-3(2H)-ylidene) |
|
Claims (13)
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
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US13/949,195 US9213248B2 (en) | 2013-07-23 | 2013-07-23 | Latex comprising colorant and methods of making the same |
JP2014139070A JP6316125B2 (en) | 2013-07-23 | 2014-07-04 | Latex containing colorant and method for producing latex |
DE102014214064.1A DE102014214064B4 (en) | 2013-07-23 | 2014-07-18 | LATEX WITH COLORANT AND METHOD OF ITS MANUFACTURING |
US14/875,131 US9580578B2 (en) | 2013-07-23 | 2015-10-05 | Latex comprising colorant and methods of making the same |
US15/341,639 US10208186B2 (en) | 2013-07-23 | 2016-11-02 | Latex comprising colorant and methods of making the same |
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US13/949,195 US9213248B2 (en) | 2013-07-23 | 2013-07-23 | Latex comprising colorant and methods of making the same |
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US13/949,195 Active 2033-12-25 US9213248B2 (en) | 2013-07-23 | 2013-07-23 | Latex comprising colorant and methods of making the same |
US14/875,131 Active US9580578B2 (en) | 2013-07-23 | 2015-10-05 | Latex comprising colorant and methods of making the same |
US15/341,639 Active 2034-04-25 US10208186B2 (en) | 2013-07-23 | 2016-11-02 | Latex comprising colorant and methods of making the same |
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US15/341,639 Active 2034-04-25 US10208186B2 (en) | 2013-07-23 | 2016-11-02 | Latex comprising colorant and methods of making the same |
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WO2016002860A1 (en) * | 2014-07-04 | 2016-01-07 | 花王株式会社 | Method for manufacturing colored particle dispersion |
WO2024038442A1 (en) * | 2022-08-14 | 2024-02-22 | Sonoviatech Ltd. | Compositions and methods for indigo dyeing |
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US5611822A (en) | 1993-05-10 | 1997-03-18 | Allegro Natural Dyes Llc | Indigo dye process |
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JPH01108554A (en) * | 1987-10-22 | 1989-04-25 | Hitachi Chem Co Ltd | Production of toner for developing electrostatic charge image |
JP2000154206A (en) * | 1998-09-18 | 2000-06-06 | Sekisui Chem Co Ltd | Dye composition, colored resin emulsion and colored fine particulate |
US6218067B1 (en) * | 1998-11-06 | 2001-04-17 | Cabot Corporation | Toners containing chargeable modified pigments |
JP2004339413A (en) * | 2003-05-16 | 2004-12-02 | Fuji Xerox Co Ltd | Process for preparing latex polymer and process for producing toner for electrostatic charge image development |
US7901859B2 (en) * | 2007-04-10 | 2011-03-08 | Xerox Corporation | Chemical toner with covalently bonded release agent |
JP2009036811A (en) * | 2007-07-31 | 2009-02-19 | Konica Minolta Business Technologies Inc | Electrophotographic toner and image forming method |
US8273516B2 (en) * | 2009-07-10 | 2012-09-25 | Xerox Corporation | Toner compositions |
JP5549579B2 (en) * | 2010-12-22 | 2014-07-16 | 日本ゼオン株式会社 | Cyan toner |
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2013
- 2013-07-23 US US13/949,195 patent/US9213248B2/en active Active
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2014
- 2014-07-04 JP JP2014139070A patent/JP6316125B2/en active Active
- 2014-07-18 DE DE102014214064.1A patent/DE102014214064B4/en active Active
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2015
- 2015-10-05 US US14/875,131 patent/US9580578B2/en active Active
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US5223368A (en) | 1991-09-06 | 1993-06-29 | Xerox Corporation | Toner and developer compositions comprising aluminum charge control agent |
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DE102014214064A1 (en) | 2015-01-29 |
US20170073499A1 (en) | 2017-03-16 |
US10208186B2 (en) | 2019-02-19 |
DE102014214064B4 (en) | 2021-09-16 |
JP2015021125A (en) | 2015-02-02 |
US20160024276A1 (en) | 2016-01-28 |
US9580578B2 (en) | 2017-02-28 |
JP6316125B2 (en) | 2018-04-25 |
US20150030977A1 (en) | 2015-01-29 |
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